Methanol → 2-Thioadenosine
Reaction equation
Cl.[NH2:2][C:3]1[N:7]([C@@H:8]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[C@H:9]2[OH:10])[CH:6]=[N:5][C:4]=1[C:17](=[N:19]O)[NH2:18].CO.[OH-].[Na+].[C:25](=S)=[S:26]>>[CH:6]1[N:7]([C@@H:8]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[C@H:9]2[OH:10])[C:3]2[C:4](=[C:17]([NH2:18])[NH:19][C:25]([N:2]=2)=[S:26])[N:5]=1Participants
5
Procedure
10.0 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide oxime hydrochloride was dissolved in 200 ml of an aqueous solution containing 175 ml of methanol, and the resulting solution was adjusted to a pH of 9 with sodium hydroxide. 50 ml of carbon disulfide was added to the solution, and the mixture was allowed to react in an autoclave at a temperature of 120° C for 5 hours under autogenous pressure (about 10 Kg/cm2) followed by working up in the same manner as described in Example 1 to obtain 9.7 g of 2-thioadenosine having a melting point of 198° C (with decomposition) in a 95% yield.
Workup
- customto react in an autoclave at a temperature of 120° C for 5 hours under autogenous pressure (about 10 Kg/cm2)
Sources & evidence
- ORD record
- ord-d63754f197804920bbc5b0992e424399
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03989682
Reaction notes
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